Effects of chelating agents on the preparation of benzenediols by oxidation of phenol with peracetic acid.

概要

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The oxidation of phenol with peracetic acid has been investigated in connection with the industrial preparation of benzenediols. The effects of 25 additives, such as derivatives of monomeric and condensed phosphoric acid, chelating agents, and salts of polybasic carboxylic acids, were examined; derivatives of condensed phosphoric acid were found to be most effective. The oxidation of phenol (213 mmol) with peracetic acid (21 mmol) in the absence of the additives gave 1,2- and 1,4-benzenediols in only 5.8% and 7.6% yields, respectively. But in the presence of 2.0×10<SUP>−7</SUP> mol of potassium diphosphate the yields of 1,2- and 1,4-benzenediol were 47% and 31%, respectively. The improvement in the yields by the additives is attributable to the masking of a trace of metals, especially iron and cobalt, present in the reaction mixture. These metals tend to catalyze the further oxidation of the benzenediols formed.
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